Jessica Stein (Jennifer Westfeldt) is a sensitive, but neurotic, New York journalist who is at the end of her emotional rope. Her brother Dan (David Aaron Baker), is engaged. Her best friend and co-worker Joan (Jackie Hoffman) is pregnant. On top of that, Jessica hasn’t dated in a year, and she can’t sleep. After an optimistic but nightmarish dating spree, which is set up by her overbearing and meddlesome mother Judy (Tovah Feldshuh), Jessica decides she needs a change in her life.
Helen Cooper (Heather Juergensen) is a fairly successful art gallery manager who is fed up with having quicky sex with various men, including her delivery guy, in various times and places. Confused about her sexual orintation, as if she thinks she may be a lesbian in denial, Helen puts a personal ad in a local newspaper asking for a date with someone. The following day, Jessica happens upon to read intriguing personal ad, whose only drawback is that it’s in the women seeking women section. On a daring whim, Jessica decides to answer it. She meets the hipster Helen at a local bar for drinks and, to her surprise, they click instantly. After going for a evening of banter, connection and heated debate about Jessica’s personal life and her repression for happiness, the discussion culminates in a kiss that Helen gives which confounds and intrigues even the reluctant Jessica.
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